Potassium Carbonate → HCID 86612826, compound

HRID 1159644Notes

Reaction equation

HRID 1159644 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl.Cl[CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>CCO.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[N:24]1([CH2:23][CH2:22][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=2)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 28310Ethyl 4-hydroxyphenylacetateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

Product 1

HCID 86612826HCID 86612826, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 702EthanolSolvent

Procedure

A solution of 1 g of ethyl (4-hydroxyphenyl)acetate in 20 ml of EtOH is admixed with 2.5 g of K2CO3, 1.68 g of 4-(2-chloroethyl)morpholine hydrochloride and 0.01 g of tetrabutylammonium iodide and then heated at reflux for 5 hours. After cooling to AT, the K2CO3 is filtered off and washed with EtOH and the filtrate is concentrated under vacuum. The residue is taken up in water and extracted with AcOEt, the organic phase is washed with water and dried over MgSO4 and the solvent is evaporated under vacuum. This gives 1.5 g of the expected compound in the form of a colourless oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. temperatureAfter cooling to AT
  4. filtrationthe K2CO3 is filtered off
  5. washwashed with EtOH
  6. concentrationthe filtrate is concentrated under vacuum
  7. extractionextracted with AcOEt
  8. washthe organic phase is washed with water
  9. dry with materialdried over MgSO4
  10. customthe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-74511b6e4bb748a7b5beac652000dda8
Source dataset
uspto-grants-2010_10
Patent number
US07812165B2

Reaction notes

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